HCID 90460303, compound → HCID 90463563, compound

HRID 1053646Notes

Reaction equation

HRID 1053646 reaction equation
[CH3:1][N:2]([CH2:10][CH2:11][N:12]([CH3:39])[CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([O:23][C:24]3[CH:29]=[CH:28][C:27]([N+:30]([O-])=O)=[CH:26][CH:25]=3)[CH:21]=2)[N:16]([CH:33]2[CH2:38][CH2:37][CH2:36][CH2:35][O:34]2)[N:15]=1)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6]>CO.[Ni]>[NH2:30][C:27]1[CH:26]=[CH:25][C:24]([O:23][C:20]2[CH:21]=[C:22]3[C:17](=[CH:18][CH:19]=2)[N:16]([CH:33]2[CH2:38][CH2:37][CH2:36][CH2:35][O:34]2)[N:15]=[C:14]3[CH2:13][N:12]([CH3:39])[CH2:11][CH2:10][N:2]([CH3:1])[C:3](=[O:9])[O:4][C:5]([CH3:7])([CH3:8])[CH3:6])=[CH:29][CH:28]=1

Participants

4

Reactant 1

HCID 90460303HCID 90460303, compound

Product 1

HCID 90463563HCID 90463563, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of (R/S) tert-butyl methyl(2-(methyl((5-(4-nitrophenoxy)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)methyl)amino)ethyl)carbamate (550 mg, 1.02 mmol, 1.00 equiv) and Raney/Ni (500 mg) in methanol (30 mL) was stirred under hydrogen at room temperature for 30 min. The catalyst was removed by filtration. The filtrate was concentrated under vacuum to give 400 mg (77%) of (R/S) tert-butyl 2-(((5-(4-aminophenoxy)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)methyl)(methyl)amino)ethyl(methyl)carbamate as a colorless oil. 1H-NMR (300 MHz, CDCl3): δ 7.52-7.49 (m, 2H), 7.33-7.26 (m, 2H), 7.18-7.12 (m, 1H), 6.90-6.80 (m, 2H), 6.71-6.61 (m, 2H), 5.70-5.68 (m, 1H), 4.11-4.09 (m, 1H), 4.07-3.91 (m, 1H), 3.79-3.73 (m, 1H), 3.71-3.33 (m, 1H), 2.79 (s, 3H), 2.57-2.52 (m, 2H), 2.49-2.17 (m, 2H), 2.17-2.05 (m, 1H), 1.80-1.68 (m, 4H), 1.42 (s, 9H) ppm.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-67e8418a9f98440691c5959815139551
Source dataset
uspto-grants-2016_07
Patent number
US09394258B2

Reaction notes

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